Markhamioside F - Compound Card

Markhamioside F

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Markhamioside F

Structure
Zoomed Structure
  • Family: Plantae - Juncaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glycoside
Canonical Smiles OC[C@H]1O[C@@H](OC(=O)c2ccc(c(c2)OC)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1OC[C@]([C@H]1O)(O)CO
InChI InChI=1S/C19H26O13/c1-28-10-4-8(2-3-9(10)22)16(26)32-17-14(13(24)12(23)11(5-20)30-17)31-18-15(25)19(27,6-21)7-29-18/h2-4,11-15,17-18,20-25,27H,5-7H2,1H3/t11-,12-,13+,14-,15+,17+,18+,19-/m1/s1
InChIKey QFNMZWPDJNEENQ-VAVDVLCISA-N
Formula C19H26O13
HBA 13
HBD 7
MW 462.4
Rotatable Bonds 7
TPSA 204.83
LogP -3.18
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.63
Exact Mass 462.14
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Juncus acutus Juncaceae Plantae 308385

Showing of synonyms

  • Awaad AS (2006). Phenolic glycosides of Juncus acutus and its anti-eczematic activity. Chemistry of Natural Compounds,2006,42(2),152-155. [View]
Pubchem: 101182651
Nmrshiftdb2: 70042128

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC(OCCC2)C2OC3CCCO3

Level: 2

Mol. Weight: 462.4 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCCCO2

Level: 1

Mol. Weight: 462.4 g/mol

Structure

SMILES: O1CCCC1OC2CCCOC2

Level: 1

Mol. Weight: 462.4 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 462.4 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 462.4 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 462.4 g/mol

Anti-eczematic

Absorption

Caco-2 (logPapp)
-6.21
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.18
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.62
Plasma Protein Binding
59.37
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.0
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.06
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.99
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.95
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-65.09
Rat (Acute)
1.98
Rat (Chronic Oral)
3.82
Fathead Minnow
3.55
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
519.31
Hydration Free Energy
-5.17
Log(D) at pH=7.4
-0.46
Log(P)
-1.7
Log S
-2.01
Log(Vapor Pressure)
-13.82
Melting Point
165.64
pKa Acid
3.62
pKa Basic
3.36
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8902
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8902
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8868
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8868
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8747
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8747
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8485
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8485
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8260
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8260
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8187
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8187
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8080
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8080
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8053
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8053
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7968
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7968
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7700
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7700
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7615
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7615
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7535
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7535
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7511
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7511
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7498
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7498
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7449
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7449
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7434
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 4 0.7434
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7431
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7431
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7367
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7367
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7349
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7349
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7327
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7327
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7307
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7307
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7262
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7262
Primosomal protein N' A6TGC5 A6TGC5_KLEP7 Klebsiella pneumoniae subsp. pneumoniae 4 0.7238
Primosomal protein N' A6TGC5 A6TGC5_KLEP7 Klebsiella pneumoniae subsp. pneumoniae 4 0.7238
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7208
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7208
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7205
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7205
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7205
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7205
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7203
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7203
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7178
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7178
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7130
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7130
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7105
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7105
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7059
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7059
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7040
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7040
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7038
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7038
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7022
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7022
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7022
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7022
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7019
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7019
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7013
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7013

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